The present invention relates to a process for producing 3,3,3-trifluoropropionaldehyde which is useful as intermediates for medical drugs and agricultural chemicals and as raw materials or synthetic intermediates for high-performance materials such as fluorine-containing polymers.
There are various reports made about the techniques for production of 3,3,3-trifluoropropionaldehyde.
Non-Patent Publication 1 discloses a process of producing 3,3,3-trifluoropropionaldehyde by converting 3,3,3-trifluoropropene into 3,3,3-trifluoro-1-propanol with the use of mercury (II) nitrate and glacial acetic acid, and then, oxidizing the 3,3,3-trifluoro-1-propanol with sodium chromate. Patent Publication 2 discloses a process of producing 3,3,3-trifluoropropionaldehyde by reacting 3,3,3-trifluoropropene with water in the presence of a palladium salt. Non-Patent Publication 2 discloses a process of producing 3,3,3-trifluoropropionaldehyde by adding trifluoromethyl iodide to ethyl vinyl ether and hydrolyzing the resulting addition product. Patent Publication 3 discloses a process of producing 3,3,3-trifluoropropionaldehyde by converting 1-chloro-3,3,3-trifluoropropene to 3,3,3-trifluoropropenyl acetate with the use of a palladium salt, sodium acetate and glacial acetic acid, and then, hydrolyzing the 3,3,3-trifluoropropenyl acetate.
Patent Publication 4 discloses a process of producing 3,3,3-trifluoropropionaldehyde by hydrolyzing alkyl 3,3,3-trifluoropropenyl ether with the use of an aqueous hydriodic acid solution.
Patent Publication 5 discloses a process of producing 3,3,3-trifluoropropionaldehyde by reacting 1-chloro-3,3,3-trifluoropropene with metal alkoxide in an alcohol (ROH) where R has a carbon number of 1 to 4, thereby obtaining CF3CH═CHOR or CF3CH(OR)2 as a reaction product, and then, hydrolyzing the reaction product in the presence of an alkane acid having a carbon number of 3 to 13. Patent Publication 1 discloses a process of producing 3,3,3-trifluoropropionaldehyde by adding trifluoromethanesulfonyl chloride to vinyl chloride, thereby obtaining 1-chloro-3,3,3-trifluoropropylacetate, and then, hydrolyzing the 1-chloro-3,3,3-trifluoropropylacetate with sulfuric acid.
Non-Patent Publication 3 discloses a process of producing 3,3,3-trifluoropropionaldehyde by reacting dimethyl-[1-(2-trifluoromethyl-3,3,3-trifluoropropenyl)]amine, which is one kind of trifluoromethyl-containing enamine, for 28 days in the presence of a magnesium sulfate hydrate.    [Patent Publication 1] Published Japanese Translation of PCT Application No. 2003-522743    [Patent Publication 2] Japanese Laid-Open Patent Publication No. 6363633    [Patent Publication 3] U.S. Pat. No. 5,777,184    [Patent Publication 4] U.S. Pat. No. 2,715,144    [Patent Publication 5] U.S. Pat. No. 6,111,139    [Non-Patent Publication 1] Journal of Fluorine Chemistry, Vol. 30, Pages 153-158, 1985 (Netherlands)    [Non-patent Publication 2] Zhurnal Organicheskoi Khimii, Vol. 25, No. 7, Pages 1376-1380, 1989 (Soviet)    [Non-Patent Publication 3] Izvestiya Akademii Nauk, Seriya Khimicheskaya, Vol. 5, Pages 1069-1071, 1997 (Russia)